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Volumn , Issue 4, 2007, Pages 628-632

Synthesis and spectral properties of a deoxyribose-phthalocyanine conjugate using a Sonogashira coupling reaction

Author keywords

Nucleosides; Palladium coupling; Photodynamic therapy; Phthalocyanines; Porphyrins

Indexed keywords

DEOXYRIBOSE; PHTHALOCYANINE;

EID: 33947286937     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967977     Document Type: Article
Times cited : (19)

References (63)
  • 11
    • 0003544982 scopus 로고    scopus 로고
    • Leznoff, C. C, Lever, A. B. P, Eds, VCH: New York
    • (d) Phthalocyanines: Properties and Applications, Vol. 4; Leznoff, C. C.; Lever, A. B. P., Eds.; VCH: New York, 1996.
    • (1996) Phthalocyanines: Properties and Applications , vol.4
  • 42
  • 60
    • 33947220481 scopus 로고    scopus 로고
    • Zinc(II) tetrakis({2-Deoxy-3,5-bis[O-(p-toluoyl, α,β- D-ribofuranosyl}ethynyl) phthalocyaninate (4, A mixture of 2 17 (250.0 mg, 0.231 mmol, 316 (524.8 mg, 1.39 mmol, Pd(PPh3)2Cl2 (20 mg) and CuI (10 mg) were dried under vacuum for 1 h. To this mixture, anhyd DMF (2.5 mL) was added followed by Et3N (1 mL) and allowed to stir at r.t. for 72 h. The solvent was removed by evaporation and the crude green solid was purified by silica gel chromatography (EtOAc-hexane, 40:60) to furnish 4 as a blue solid (360.0 mg, 75, IR (KBr, 2954, 2229, 1720, 1611, 1488, 1386, 1271, 1178, 1100, 1020, 837, 752 cm-1; 1H NMR (600MHz, acetone-d6, δ, 8.64 (br s, 8 H, Ar-H, 8.23-8.06 (m, 20 H, Ar-H, 7.42-7.37 (m, 16 H, Ar-H, 5.87-5.56 (m, 8 H, 1′,3′-H, 4.95-4.71 (m, 12 H, 4′,5′-H, 3.11-2.98 m, 8 H, 2′-H, 2.46-2
    • 4].
  • 61
    • 33947238455 scopus 로고    scopus 로고
    • Zinc(II) tetrakis[(2-deoxy-α,β-D-ribofunosyl)ethynyl] phthalocyaninate (1, A mixture of 4 (20.1 mg, 0.0096 mmol, and K2CO3 (14.4 mg, 0.104 mmol, in MeOH-THF (2:1, 3 mL) was stirred at r.t. for 48 h. The reaction mixture was filtered and washed with MeOH. The MeOH was evaporated off to furnish a dark blue solid, to which was added H2O (4.0 mL, pH adjusted to 6) and filtered. The solid was washed with H2O and 30% of acetone in H2O and purified twice by Sephadex® G-25 using MeOH as an eluent. Evaporation of the solvent gave a crude blue solid. Further purification by recrystallization with MeOH and EtOAc gave pure 1 (8.2 mg, 80, IR (KBr, 2954, 2229, 1720, 1611, 1488, 1386, 1271, 1178, 1100, 1020, 837, 752 cm-1; 1H NMR (600MHz, CD3OD, δ, 8.54 (br s, 8 H, Ar-H, 7.91 (br s, 4 H, Ar-H, 5.31 (br s, 4 H, 1′-H, 4.52 (br s, 2 H, 4′-H, 4.43 br s
    • -5 M).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.